


Payback's a Bitch

by orphan_account



Category: Supernatural
Genre: Anal Sex, Chair Bondage, Cock Cages, Dom/sub, Fucking Machines, M/M, Orgasm Delay/Denial, Sex Swing, Sex Toys, Switching, Teasing
Language: English
Status: Completed
Published: 2015-10-27
Updated: 2015-10-27
Packaged: 2018-04-28 12:08:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,401
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5090144
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>In which Dean and Castiel get some inspiration from the glorious world wide web and it ends in fun and frustration for both of them.</p>
            </blockquote>





	Payback's a Bitch

**Author's Note:**

> Yes, this is actually (loosely) based on a post I saw online. I just spend too much time on porn websites, okay?

Castiel kind of regrets showing Dean that website. He’d been browsing the web when he stumbled across the post and it seemed like something they could try, which is why he asked Dean for his opinion. He said yes. The idea wasn’t overly complicated, both of them were supposed to wear cock cages for a week and then try to orgasm at the same time once the seven days were over.

They’ve made it through all seven days without having sex or getting off and Castiel groans internally when he thinks about the many frustrating make-out sessions that had led to. It’s even worse when he thinks about how they slightly changed the rules. Dean had suggested that instead of getting to come at the same time, they could make things a bit more interesting and Castiel – at the time thinking it would be a good idea – agreed. After a short discussion they decided that one of them would already get to come on Saturday, the other would have to wait until Sunday. The catch was that the person who gets released would be the sub that day.

Now it’s Friday and in a miraculous turn of events, Dean just beat Castiel at Rock-Paper-Scissors, which means he already gets to come tomorrow. He seems stupidly excited about it and spends the rest of the day teasing Castiel, who can’t help but be grumpy. He lets Dean enjoy his victory while he silently makes plans for tomorrow. The good thing about the situation is that Dean is going to be his sub tomorrow and just because he’s won doesn’t mean Castiel is going to make it easy for him. Quite the opposite actually. Some serious teasing and denial are in order and Dean doesn’t seem to be as concerned about that as he should be.

On Saturday morning, Dean doesn’t even bother getting dressed and except for the cage he’s only wearing the collar Castiel put on him after they got up. It’s a beautiful sight and it gets even better when Dean starts to get annoyed and fidgety when they don’t do anything after breakfast.

“Cas? You know I get to come today, right? Don’t you want to take this off?”

Dean is cupping his own caged cock in his hand and Castiel glances down at it before he looks back up and grins.

“I know. But we didn’t agree on when exactly you get to come so technically, I could keep you waiting until midnight. Remember, I’m your Dom so I make the decisions. Now get out of the way, I need to clean these dishes.”

Dean pouts as he stalks off and out of the corner of his eye, Castiel sees him settling down on the couch with his laptop. The rest of the morning is uneventful, Dean keeps grumbling and making unintelligible noises that sound like complaints while Castiel calmly does chores around the house.

Lunch comes and goes and it’s early afternoon when Castiel starts putting his plan into action. Dean is still in the living room doing his thing and Castiel goes upstairs to grab everything he needs. He comes back downstairs carrying leather cuffs, rope, nipple clamps, a gag, a towel, lube and a vibrating plug. When he steps into the living room, Dean turns around and his eyes go almost comically wide at the sight before he jumps up and positions himself in front of Castiel, ready to receive his orders. He obediently waits until Castiel has brought a chair from the kitchen, positioned it in front of the TV and placed the towel on it.

Dean lets himself be prepared without making a fuss but Castiel can sense that he’s getting nervous and he’s almost ashamed of how much he loves that. After he’s opened Dean up and plugged him, Castiel ties him to the chair. He uses the leather cuffs to secure Dean’s wrists behind the back of the chair and then grabs the rope to tie his torso and thighs to the chair too. Dean’s ankles are next and Castiel takes another length of rope to tie them to the legs of the chair. Like that, Dean’s movements are pretty limited and he hisses when Castiel puts the nipple clamps on him. The ball gag comes last and when that’s done, Castiel steps back and reaches into his pocket, smirking when he pulls out the key to the cage.

“Now let’s get that thing off you.”

Dean is clearly relieved when his cock slips free but Castiel can also sense just how nervous Dean’s getting and all he can think is ‘good’. There’s only one piece missing now and Castiel wanders over to where his own laptop is sitting on a drawer and takes out the DVD he’s spent most of last night and this morning preparing. Once he’s inserted it into the DVD player and pressed play, he turns around to Dean.

“Have fun watching this, I’m gonna be in the kitchen doing some work.”

He relishes in the distressed sounds Dean makes when he realizes what he’s about to see. Castiel is not ashamed to admit that he and Dean filmed a lot of their sexual adventures and he’s taking full advantage of that now. He chose the best scenes he could find, clips of himself getting fucked, of Dean getting fucked and of both of them involved in all kinds of situations, be it a prostate massage or an edging session. Of course Castiel also made sure to include lots of shots of either of them having an orgasm. He’s put together enough material for at least three hours and Dean is already squirming and pleading behind the gag when Castiel grabs his laptop and stops in the doorway to look over his shoulder.

“Don’t you dare look away.”

With that, he leaves. While Dean seems to be freaking out about the situation he’s found himself in, Castiel makes himself comfortable in the kitchen. He chooses a spot at the table that allows him to see into the living room so that he can see if Dean needs to use his safeword. For the time being, he leaves Dean to his misery and opens up his laptop.

About half an hour in, Castiel takes the remote to the vibrating plug out of his pocket and just stares at it for a few moments. In the end he decides that the best way to torture Dean is to turn it on and off again in random intervals and always keep it on the lowest setting. He knows that it won’t be enough to get Dean off, especially since he can’t move properly because of the ropes. The first time Castiel turns on the plug, he can hear a high pitched whine from the living room and he smiles to himself. This is going even better than expected.

Over the next two hours, Castiel keeps turning the vibrator on and off and it results in all kinds of interesting noises coming from Dean. Other than that, the moaning coming from the TV is the only sound in the house and Castiel is not entirely unaffected himself. He tries not to let it get to him and ignore how his cock is pressing against the metal bars of the cage.

When Castiel finally goes back into the living room he’s greeted with a wonderful sight. There are tears in Dean’s eyes and on his cheeks, he’s drooling around the gag, and his cock is rock hard and a perfect shade of dark red. Castiel almost feels bad about not giving him any relief yet but he shakes his head at the hopeful look directed at him and kneels next to the chair, ignoring Dean’s whining. He doesn’t do anything at first, just watches the TV and he really wishes he could get off. As it is, he’s still locked and takes his frustration out on Dean.

Castiel starts by turning the vibrations on again and this time he can properly see how Dean twitches and squirms in his bonds. He spends about five minutes amusing himself by constantly turning the plug on and off again and when it gets too repetitive for him, Castiel reaches out and gently brushes his fingertips against Dean’s hard cock. He’s rewarded with a high pitched moan that turns into a sob when he immediately pulls away again.

Castiel stops paying attention to the TV and instead focuses on Dean’s reactions while he alternatively uses the plug and his hand. There are more tears running down Dean’s face now but, Castiel has to hand it to him, he never looks away from the TV, no matter what Castiel does. At one point he pulls off the clamps and Dean groans in pain but is quickly distracted from it by a clip of himself riding Castiel while he’s wearing his cowboy boots.

The teasing continues for a while longer before Castiel finally decides it’s enough when a scene of him blowing Dean starts on the TV. He tries to copy it and moves until he can kneel in front of Dean who is nodding frantically. After a few moments of considering what to do, Castiel decides to just go for it and he swallows as much of Dean as he can without wasting any time on teasing licks or kisses. Even the gag can’t muffle the loud moan coming from Dean and it just encourages Castiel to go faster. He knows the blowjob that’s currently on screen lasted a long time because he kept teasing Dean but that’s not his intent now. Dean is already close to orgasm anyway and Castiel helps him get there as best as he can, bobbing his head and using his tongue to play with the slit just the way Dean likes it. He swallows everything and then looks up to see Dean slumped in his bonds, breathing heavily. Castiel turns off the TV, not bothering to take out the DVD, before he unties Dean.

“You’re so good for me, Dean. So beautiful.”

Dean doesn’t comment, just smiles dopily and lets Castiel help him go upstairs and into the bathroom to clean up. Some time later, when they’re both sitting in the bathtub, Dean leans his head back on Castiel’s shoulder and murmurs into his ear. “I hate you.”

Castiel snorts and gives Dean a peck on the cheek. “No, you don’t.”

Dean grins as he turns onto his stomach so he can look Castiel in the eye. “True. But you do remember that it’s my turn tomorrow, right?”

This doesn’t sound good but Castiel tries to sound nonchalant when he answers. “I’m aware.”

Dean seems to know that he’s making Castiel nervous and his grin turns even more mischievous. “Good.”

 

~*****~

 

What the hell was he thinking when he gave Dean this gift? True, it was on sale and something Dean (and Castiel too if he’s honest) was interested in but this is definitely not what he wanted.

Castiel is lying in the sex swing he bought Dean for his birthday and he’s once again regretting his life decisions. There’s a collar around his throat, his feet and legs are held up by leather slings which leaves him completely exposed and his hands are tied somewhere above his head. On top of that he’s also gagged, blindfolded, and his cock is still locked up.

And because that apparently wasn’t enough, Dean is also putting the fucking machine to good use. It’s on the lowest setting and the thrusts are gentle and agonizingly slow but if Castiel moves just right, he can get it to press against his prostate. Still, it doesn’t help because he’s locked up and due to the slow movements there’s not enough stimulation to get him off anyway. It is enough to get him hard though, but only until the pain of his erection trapped in the cage becomes too much and his cock softens again, just to start the whole cycle anew.

Castiel groans in frustration when the machine hits the right spot again. The swing is moving slightly due to the thrusts and Castiel just lets it happen and hopes he manages to get into the right position by chance. He tries not to move too much himself because with the fucking machine in play, the risk of hurting himself is too big. Castiel doesn’t know where Dean is, what he’s doing or how long they’ve been here.

Dean came to him a few times and used a brush and feathers to caress the parts of Castiel’s cock that are accessible through the bars of the cage. It tickled and hurt at the same time and left Castiel a moaning mess. He just lies there and takes it, both the teasing touches and the dildo fucking him. Begging wouldn’t do him any good, he knows Dean won’t change his mind. Castiel lies there, slowly swinging back and forth for what feels like ages before he hears some rustling and footsteps nearby and the blindfold is pulled off.

The picture that he’s greeted with makes Castiel’s mouth go dry and he can’t suppress a small whine. Dean is completely naked except for a pair of pink panties that already have a wet patch on the front. He doesn’t untie Castiel, but he does unlock the cage and although it feels heavenly, Castiel tries not to get too excited because there’s probably more to come.

Apparently he’s right because Dean goes to the bed and smirks at Castiel as he lies down. That they installed the swing so it’s facing the bed comes in handy now and Castiel gets to watch as Dean sprawls out seductively on the bed and starts rubbing his cock through the panties while one of his hands comes up to pinch his nipples. In addition to this hot sight there’s still the machine relentlessly thrusting into him and Castiel can feel his cock getting hard. Unfortunately, he can’t do more than moan and watch, twitching in his bonds and wishing that he could participate.

Things get even worse when Dean finally pulls the panties to the side and reveals his hard and leaking cock (not that it was very well hidden by the thin lacy material). It’s glistening from all the precome and if it wasn’t for the gag, Castiel would lick his lips. Dean doesn’t acknowledge him as he wraps a hand around his own cock and gives a few firm strokes, moaning and thrusting into his fist. Castiel, still pathetically swinging back and forth, just wants to cry.

Suddenly Dean looks right at him and smirks, then reaches behind himself for something that’s hidden under the pillow and the vibrations start a second later. Castiel squeezes his eyes shut and moans. He hadn’t realized that Dean used one of the vibrating dildos with the machine and he’s not sure he can deal with that. It’s on the lowest setting, just like the machine but it’s more than enough to make him whimper and squirm whenever it hits his prostate.

Dean ignores that and goes back to playing with himself. He gives his cock slow strokes that make his legs visibly tremble and Castiel stares transfixed at the point where the head peaks out of Dean’s fist before it disappears again. It’s mesmerizing to watch and Castiel almost doesn’t notice what Dean’s other hand is doing. Apparently Dean has grown bored of tugging at his nipples and instead he’s cupping his balls now, tugging and gently squeezing them.

Eventually he starts alternating between them and his nipples while his other hand stays firmly wrapped around his cock. All of it is accompanied by throaty moans and the occasional hiss when Dean is being particularly rough with himself. It’s still nothing compared to the noises Castiel is making and when he tears his eyes away from Dean for a second to look at himself he whimpers when he sees how much precome his cock is leaking against his stomach. A little further down, the machine is still thrusting in the same constant rhythm and the vibrations are making it even more frustrating.

Meanwhile, Dean has his head thrown back and seems completely lost in sensation since he is properly fucking his fist now and keeps rubbing his nipples that already look red and sore. It’s a beautiful display that Castiel would be grateful for any other time but right now he really just wants to come and he moans brokenly. Thankfully, Dean seems to take pity on him and when he stops touching himself he stays on the bed for a few moments, catching his breath, before he gets up and walks over to the swing. Castiel sighs in relief when he turns off the vibrations and the machine and Dean smiles at him as he puts the toys away.

“You okay?”

Castiel nods and tries to smile back despite the gag in his mouth and Dean laughs as he leans down to kiss his forehead. “Good.”

There’s a small moment where Castiel panics because Dean turns around and walks away but he relaxes when he sees Dean grabbing the lube from the bedside table. Dean quickly spreads a bit of it inside of Castiel with his fingers before slicking up his own cock and pushing in. The machine made prepping pretty much unnecessary but Dean is still a tiny bit thicker than the dildo and Castiel doesn’t breathe until Dean is fully inside of him and groans.

“Jesus Christ, how are you still so tight even after the machine’s been fucking you? Fuck, I love it.”

Castiel lets out an undignified squeak when Dean grabs his hips and smirks. “Let me hear you.”

And Castiel obeys. How can he not, with the rough pace that Dean sets? True, it’s not the hardest or fastest he can go because he’s holding back, not wanting to damage the swing that’s already creaking ominously, but it serves his purpose and makes Castiel scream in pleasure. It feels amazing to finally have Dean inside of him, especially when he manages to hit Castiel’s prostate and sends sparks of pleasure through his body. The movements of the swing just enhance the pleasure as Dean uses it to pull Castiel back onto his cock while he simultaneously pushes in.

The sound of flesh slapping against flesh fills the room along with Dean’s ragged breathing and Castiel’s moans, but as good as it is, it’s not enough. Despite his best efforts, Castiel has not yet managed the art of anal orgasms and luckily Dean knows it and helps him out by wrapping a hand around his cock. He strokes it in time with his thrusts and rubs the head, using the precome there to ease the way. With the added stimulation it doesn’t take much longer for Castiel to come and he cries out as he shoots his load all over his own stomach and chest. Dean helps him through his orgasm and only lets go when Castiel gets too sensitive and starts whimpering.

While Castiel slowly comes down from his orgasm, Dean can focus on his own pleasure and it seems like he’s been close too because he picks up speed and comes after a few more thrusts, spilling inside of Castiel with a breathless moan. There are a few moments of silence after that where they’re both just breathing hard and stare at each other. Eventually Dean pulls out and smiles. “That was amazing.”

Castiel can only agree and he nods happily. The gag is the first thing to go before Dean unties Castiel and helps him stand up, legs still wobbly after his orgasm and the time he spent lying in the swing. They don’t take a bath today and settle for a quick shower before they go back to bed and cuddle up together under the blankets. They trade kisses for a few minutes and then Dean pulls away and reaches over to the bedside table to grab the cock cage. He turns it over in his hands a few times before he looks up at Castiel and smiles shyly.

“Can we do that again?”

Castiel isn’t sure whether he’s only referring to the chastity or also to all the other stuff they did but he’s on board with it either way and he grins.

“Definitely.”


End file.
